High-performance liquid chromatographic determination of some anthraquinone and naphthoquinone dyes occurring in historical textiles

Novotná, Petra; Pacáková, Věra; Bosáková, Zuzana; Štulı́k, Karel

doi:10.1016/s0021-9673(99)00980-2

Cited by 107 publications

(34 citation statements)

References 24 publications

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“…Notably, the glycosidic compounds showed by far the largest peaks suggesting that they are much more abundant in the plant that the aglycon derivatives shown to be 236.8:1 mg cm -3 glycoside concentration to alizarin in the ethanol extract. Hence if there is no further treatment to the dyebath then the main colorant components are the glycosides, and not the aglycons which is often inferred in other publications (Liu et al, 2011, Novotna et al, 1999.…”

Section: Resultsmentioning

confidence: 81%

Isolation and extraction of ruberythric acid from Rubia tinctorum L. and crystal structure elucidation

2015

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Madder (Rubia tinctorum L.) has been exploited as a dye throughout history. The roots of the plant are very rich in the highly coloured glycosidic compounds ruberythric acid and lucidin primeveroside, alongside the corresponding aglycons which can be readily formed by deglycosylation, particularly during extraction. Supported by 1 H and 13 C NMR data, the conclusive X-ray crystal structure of the natural dye ruberythric acid is presented for the first time. The solid state structure revealed extensive intermolecular hydrogen bonding interactions between the sugar moieties in the unit cell, but only intramolecular hydrogen bonding through the hydroxyquinone groups. There is also some additional -stacking from the anthraquinone moiety.

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Section: Resultsmentioning

confidence: 81%

Isolation and extraction of ruberythric acid from Rubia tinctorum L. and crystal structure elucidation

2015

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“…Dye analysis is usually performed by liquid chromatography with a diode array detector [6][7][8][9][10][11], but nowadays, mass detection is becoming increasingly important [12][13][14][15][16][17][18][19][20]. A successful approach to identify natural dyes requires that, prior to the chromatographic analysis, an adequate analytical methodology is used for their extraction from the textile fibres.…”

Section: Introductionmentioning

confidence: 99%

“…Concentrations of the yarn extracts were measured with the photometry function on the UV-Vis spectrophotometer, and the authors found that although being as powerful as the conventional HCl method, the H 2 EDTA/DMF extraction Fig. 1 Chemical structures of the major chromophores of the studied natural dyes: (1) woad, (2, 3, 4) weld, (5, 6) brazilwood, (7,8) logwood, (9) cochineal and (10, 11) madder protocol preserves the fibre structure for further investigation. In the same period, Kirby and White [23] suggested a method involving the use of a boron trifluoride/MeOH mixture for the extraction of lake pigment dyestuffs from paintings, and the same procedure was used a few years later [24] to extract dyestuffs from purple samples in a fifteenth century velvet panel.…”

Section: Introductionmentioning

confidence: 99%

Extracting natural dyes from wool—an evaluation of extraction methods

et al. 2011

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The efficiency of eight different procedures used for the extraction of natural dyes was evaluated using contemporary wool samples dyed with cochineal, madder, woad, weld, brazilwood and logwood. Comparison was made based on the LC-DAD peak areas of the natural dye's main components which had been extracted from the wool samples. Among the tested methods, an extraction procedure with Na 2 EDTA in water/DMF (1:1, v/v) proved to be the most suitable for the extraction of the studied dyes, which presented a wide range of chemical structures. The identification of the natural dyes used in the making of an eighteenth century Arraiolos carpet was possible using the Na 2 EDTA/DMF extraction of the wool embroidery samples and an LC-DAD-MS methodology. The effectiveness of the Na 2 EDTA/DMF extraction method was particularly observed in the extraction of weld dye components. Nine flavone derivatives previously identified in weld extracts could be identified in a single historical sample, confirming the use of this natural dye in the making of Arraiolos carpets. Indigo and brazilwood were also identified in the samples, and despite the fact that these natural dyes were referred in the historical recipes of Arraiolos dyeing, it is the first time that the use of brazilwood is confirmed. Mordant analysis by ICP-MS identified the widespread use of alum in the dyeing process, but in some samples with darker hues, high amounts of iron were found instead.

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“…[1] Beside their potential applications as safe and ecofriendly natural colorants in foods, drugs, cosmetics, and textiles, [2][3][4] their use has been extended as chemical sensors, [5] organogelators, [6] liquid crystals, [7][8][9][10][11] and DNA photooxidants. [12] Moreover, anthraquinones are well known to be the major active components in many traditional Chinese medicinal herbs.…”

Section: Introductionmentioning

confidence: 99%

“…[37] For that reason, the installation of this moiety was one of the main tasks in our synthetic approach. As carrier for this pharmacophoric group we have chosen the anthraquinone natural products chrysophanol (2) and islandicin (3), which both show a distinct similarity to the structural core of mensacarcin (1). Thus, islandicin (3), having the epoxide side chain attached in the C2 position, can be regarded as an aromatized analog of mensacarcin.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Highly Functionalized Anthraquinones and Evaluation of Their Antitumor Activity

2007

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Highly functionalized anthraquinones which derive from the natural products mensacarcin, islandicin, and chrysophanol have been efficiently synthesized using a Diels–Alder reaction as key step. The introduction of the proposed pharmacophoric side chain unit has been achieved by an addition of an aryllithium species onto different aldehydes. Furthermore, the antitumor activity of these novel compounds has been studied by the in vitro growth inhibition of human lung carcinoma cells of line A549.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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High-performance liquid chromatographic determination of some anthraquinone and naphthoquinone dyes occurring in historical textiles

Cited by 107 publications

References 24 publications

Isolation and extraction of ruberythric acid from Rubia tinctorum L. and crystal structure elucidation

Isolation and extraction of ruberythric acid from Rubia tinctorum L. and crystal structure elucidation

Extracting natural dyes from wool—an evaluation of extraction methods

Synthesis of Highly Functionalized Anthraquinones and Evaluation of Their Antitumor Activity

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